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Merck

B4563

Sigma-Aldrich

Bisantrene dihydrochloride

≥98% (HPLC)

Synonym(e):

Bis((4,5-dihydro-1H-imidazol-2-yl)hydrazone)-9,10-anthracenedicarboxaldehyde dihydrochloride, NSC 337766

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About This Item

Empirische Formel (Hill-System):
C22H22N8 ·2HCl
CAS-Nummer:
Molekulargewicht:
471.39
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥98% (HPLC)

Form

solid

Lagerbedingungen

desiccated

Löslichkeit

deionized water: 8 mg/mL

Lagertemp.

room temp

SMILES String

Cl.Cl.C1CN=C(N1)N\N=C\c2c3ccccc3c(\C=N\NC4=NCCN4)c5ccccc25

InChI

1S/C22H22N8.2ClH/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22;;/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30);2*1H/b27-13+,28-14+;;

InChIKey

KINULKKPVJYRON-PVNXHVEDSA-N

Anwendung

Bisantrene (NSC 337766), and its derivatives are topoisomerase II poisons and DNA intercalators. It may be used as model compounds to study P-glycoprotein-mediated multiple drug resistance (MDR1). Bisantrene may be used as a Rac1 inhibitor.

Biochem./physiol. Wirkung

Bisantrene dihydrochloride is an antineoplastic agent, MDR1 substrate, DNA intercalator, and topoisomerase II poison. Cancer cells that develop resistance to bisantrene tend to overexpress P-glycoprotein. Bisantrene can be used to select for P-glycoprotein-mediated multiple drug resistance. The data suggest that bisantrene is an excellent substrate for P-glycoprotein.
Bisantrene is an anthracene bishydrazone derivative, which has antitumor activity.

Piktogramme

Exclamation markEnvironment

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Acute Tox. 4 Oral - Aquatic Acute 1

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Die Dokumentenbibliothek aufrufen

Disposition of bisantrene in humans and rabbits: evidence for intravascular deposition of drug as a cause of phlebitis
Powis G and Kovach JS
Cancer Research, 43(2), 925-929 (1983)
V I Salianov et al.
Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic], 35(1), 19-22 (1990-01-01)
The effect of anthrachinone and anthracene derivatives on linear and circular superstranded molecules of DNA in conditions of their condensation was studied. It was shown that the compounds formed strong intercalation complexes with the molecules of the linear and circular
S Venitt et al.
Journal of medicinal chemistry, 41(19), 3748-3752 (1998-09-11)
Fifteen anthracene-9,10-dione ("anthraquinone") derivatives with (omega-aminoalkyl)carboxamido substituents at the 1-, 2-, 1,4-, or 2, 6-ring positions were tested for bacterial mutagenicity in reverse-mutation assays using Salmonella typhimurium frameshift strains TA1538, TA98, and TA97a, in the presence and absence of a
C Sissi et al.
Molecular pharmacology, 54(6), 1036-1045 (1998-12-18)
To elucidate structure-activity relationships for drugs that are able to poison or inhibit topoisomerase II, we investigated the thermodynamics and stereochemistry of the DNA binding of a number of anthracene derivatives bearing one or two 4, 5-dihydro-1H-imidazol-2-yl-hydrazone side chains (characteristic
G Visani et al.
Haematologica, 75(6), 527-531 (1990-11-01)
In vitro clonogenic assays may be useful for determining the sensitivity of leukemic cells to chemotherapeutic agents. We evaluated the antileukemic effect of Bisantrene (an anthracene derivative now undergoing phase II clinical trials in relapsed/resistant acute non lymphoid leukemias-ANLL) using

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